Getting close! I have made a few changes to our very ambitious itinerary since I posted the above:

In Carriacou, we are thinking of anchoring at paradise beach instead of Sandy Cay. if you are following sunset Sammy's thread that's the beautiful beach where he is staying. It is more accessible than Sandy Cay which requires a bit of a dingy ride (especially with 8 adults!) There may be more options for mooring balls for three boats than Sandy Cay which might be full when you get there. something to consider. Also there is are multiple bars on the beach!

Bequia may be unrealistic for our shorter itinerary and if you have 10 days on the boat then I would take your time and check in at Union and then crawl up through Tobago, Mayreau, etc. Would be better and an easier sail from Mayreau for you than leaving direct from Carriacou which would be a tough sail. You also wouldn't have to do a check-in at prickly pear island, you sail from becquia to Union clear out and then check in at Union island and explore. Nice down wind sail from Carriacou to Port St Louis.

Cheers!